Crowning glory: The art of Kentucky Derby hats

By Ashley Strickland, Special to CNN

Updated 1443 GMT (2143 HKT) May 4, 2012

Hats off to the races20 photos

Hats off to the races – You may not be able to spot every single hat at the Derby, but four milliners shared their custom designs with us. Sally Faith Steinmann of Maggie Mae Designs created this hat in honor of Arson Squad, a retired race horse, who belongs to the Old Friends of Kentucky, a facility for retired thoroughbreds. The hat was auctioned to raise money and awareness for the foundation. Steinmann's love of horses inspires her designs.

Hide Caption

1 of 20

Hats off to the races20 photos

Hats off to the races – Steinmann's "Michaela" hat uses dupioni silk to create a wide brim hat, as well as a large rose curl, and one of her trademarks, several silk organza "feathers." She doesn't like to use real feathers.

Hide Caption

2 of 20

Hats off to the races20 photos

Hats off to the races – Vintage netting, featured on designs like Steinmann's "Marguerite" hat, is still a favorite among the Derby crowd, as is her use of pleated satin.

Hide Caption

3 of 20

Hats off to the races20 photos

Hats off to the races – This "Candy" creation by Steinmann showcases the bright pinks and flowers that Derby-goers love, like the fabric peony that dominates this wide brim design.

Hide Caption

4 of 20

Hats off to the races20 photos

Hats off to the races – The ruffled edges of Steinmann's "Jamie" hat have long been a tradition at the Derby, as well as the braiding and bows that adorn the top.

Hide Caption

5 of 20

Hats off to the races20 photos

Hats off to the races – Diane Siverson, of Lady Diane Hats, is proud of her "Morning Star" hat. The design inspires her customers to order similar customized hats.

Hide Caption

6 of 20

Hats off to the races20 photos

Hats off to the races – Siverson's "At the Races" fascinator is one example of how milliners took the trend, popularized and worn largely at the 2011 Derby, and gave it new life.

Hide Caption

7 of 20

Hats off to the races20 photos

Hats off to the races – A classic Derby design, Siverson's "Triple Crown" hat, is piled high with feathers and floral motifs. Large hats full of feathers are a nostalgic reminder of past years.

Hide Caption

8 of 20

Hats off to the races20 photos

Hats off to the races – Siverson's special wire design within the brim of each of her hats allows for them to be easily reshaped once customers receive them. This "Gentle Breeze" hat showcases her characteristic "sexy swoop."

Hide Caption

9 of 20

Hats off to the races20 photos

Hats off to the races – Siverson's customers call her hats, like this "Ocean Mist" design, a "party in a box" because she uses balloons to stabilize the hats within their boxes when she ships them.

Hide Caption

10 of 20

Hats off to the races20 photos

Hats off to the races – Gena Conti, of Gena Conti Millinery, is proud that her "Spectator Roses" hat is housed in the Kentucky Derby Museum at Churchill Downs. It won the museum award for "Most Representative of the Kentucky Derby."

Hide Caption

11 of 20

Hats off to the races20 photos

Hats off to the races – Conti's "Bed of Roses" hat is made from sinamay, a plant-derived straw-like fabric that involves shaping and stabilizing over wooden blocks.

Hide Caption

12 of 20

Hats off to the races20 photos

Hats off to the races – Conti says she is a "frustrated sculptor," so she likes to create angles and volume in her designs, like this "Tracey Luinda" hat.

Hide Caption

13 of 20

Hats off to the races20 photos

Hats off to the races – One of Conti's best-selling designs is the "Where's Robin?" fascinator. She has styled it in different colors to match her varied clients.

Hide Caption

14 of 20

Hats off to the races20 photos

Hats off to the races – Animal prints are often a trend spotted at the Derby, where they are usually adorned with similar accents like these zebra stripe dyed feathers on Conti's "Where the Wild Things Are" hat.

Hide Caption

15 of 20

Hats off to the races20 photos

Hats off to the races – The bigger, the better! Jill Henning's wide brims are easy to spot, and she watches for them on Derby day.

Hide Caption

16 of 20

Hats off to the races20 photos

Hats off to the races – Accent feathers make a statement all their own, and they can be used to decorate fascinators or Henning's angled wide brims.

Hide Caption

17 of 20

Hats off to the races20 photos

Hats off to the races – Every milliner is inspired by something else in their life, and for Henning, it's roses. She grows more than 100 rose bushes in her backyard and garden.

Hide Caption

18 of 20

Hats off to the races20 photos

Hats off to the races – The great thing about a wide brim? No matter the weather at the Derby, if the sun is out, you're completely shaded by your own hat, like this bright wide brim from Henning.

Hide Caption

19 of 20

Hats off to the races20 photos

Hats off to the races – The big, floppy Southern-style hat, with a round crown, is a perennial favorite for Derby-goers young and old.

Hide Caption

20 of 20

Story highlights

Other attractions may draw spectators to the Kentucky Derby, but the hats reign supreme

Milliners make custom bespoke hats, from fascinators to wide brims, for each customer

This business has become a passionate second career for each of them

During the 138th annual "Greatest Two Minutes in Sports," bets will be lost, hearts will break and mint juleps will be sipped, but for many spectators at the Kentucky Derby and elsewhere, "It's all about the hats." And it's a time for the artists who craft these hats to sit back, rest their exhausted hands and look for their creations among the crowds on TV.

But it's the moment when a woman carefully removes her crown from the clouds of hatbox tissue and places it at just the right angle, the brim dipping down alluringly over one eye and reaching up to the heavens at the other end, that she and her hat embody the same intriguing personality.

"My husband's mother went to the Derby when she was a teenager -- she's 98 years old -- and she remembers the sea of hats. In our culture, we don't have all that many occasions like this. There is nothing like it, from the infield to Millionaire's Row."

Breeding Kentucky Derby studs

Just Watched

Female jockey aims to win Derby

Any woman wearing the right hat can feel like queen for a day at the Derby event of her choice. Perhaps it is an escape from her daily life, or even daily persona, that lies behind the feminine mystery of Derby millinery.

From towering fascinators to 25-inch-wide Southern sloping brim hats, all adorned with an array of feathers, bows or giant flowers, each topper has a story to tell about the classically chic or flamboyantly bold woman wearing "her." The hat is too special to be an "it," Steinmann said.

While so many great traditions associated with the Derby, like the hats, largely stay the same, there is one constant unknown: the weather. If it rains, don't be surprised to witness a sea of bobbing plastic bags shielding these prize hats from the elements. After all, the custom creations will become heirlooms, passed down for generations.

It is why these hats, and their wearers, cause spectators at the Derby to take pause, snap photos and vote for them in contests. Some hats even wind up in the Kentucky Derby Museum at Churchill Downs. The colorful headpieces are also on display at the Kentucky Oaks, the "little sister of the Derby" race on Friday, as well as races like the Belmont Stakes and Preakness, or parties, high teas, luncheons and charity events planned around race season.

For the women who craft and sell these soft sculptures, hat-making is an intimate art form relying on the intricately plaited bond of creativity and tradition. For a true milliner, none of the hats is bought and spruced up -- these women are starting from scratch.

"I love making the bodies of the hat out of the silk dupioni, but then when it gets to trimming the hat, and I can actually take a strip of fabric and weave it, wind it and swirl it up with silk organza into a rose curl or a Marguerite, and I feel like a sculptor," Steinmann said.

In the same way a painter communicates with a custom palette, Steinmann and other designers speak fabric. They work with ruffles, layers, buttons, swirls, crinkles, rosettes and "feathers that dance in the sunlight" to create dazzling combinations of texture and hue that define the singular woman who requests one.

"It's the one time you can feel that you are in the lap of luxury," Detroit milliner Gena Conti explained. "It is an excuse. And sometimes we need an excuse to step outside ourselves and do something that we really want to do all along."

One of Conti's clients is celebrating her 30th birthday on Derby day. The woman had a choice: She could spend her money on great box seats for the Derby or buy outrageous hats. She bought mediocre seats and called Conti, asking for two hats.

Just how extreme is "outrageous"? Bespoke Derby hats and fascinators can cost anywhere from $135 to thousands, depending on the labor, materials and design.

Some milliners believe the average range to be between $300 and $500. But accents like ostrich feathers can be expensive on their own; not to mention Parisian silk hand-pleated ribbon, which can cost Conti $800 a spool.

Milliners are generally happy to work within a budget, but why are women willing to pay thousands for a hat that they may wear only a few times, or just once? Even if they can wear the hat to another race or luncheon, it won't be seen at another Kentucky Derby.

"People won't do it," said Diane Siverson, owner and milliner of Lady Diane Hats in Idaho. "I have a customer that buys one every year. They wouldn't dream of wearing it again -- it just isn't done."

But the hat is a memory, an heirloom and a work of art that is uniquely hers, Steinmann said. The Derby is a once-in-a-lifetime experience for some, because the expenses can add up quickly.

"People tell me 'I'll never get to do this again,' and I hear this time and time again, 'This is on my bucket list, and if I'm going to do it, I'm going to do it right,'" Siverson said.

While women preparing for the Derby or other events can look within their city for a milliner, many customers turn to searching online, which is how they find designers like Conti, Siverson, Steinmann and Jill Henning of Jill Henning Fineries, based in Toledo, Ohio.

"I never started this for money. I started because I love to create," Henning said. "The inspiration comes from everywhere."

For these women, millinery has become a second career, born out of a shared epiphany: "I want to make hats!"

They each took classes, apprenticed under other hat makers or worked off of a basic sewing knowledge and taught themselves millinery.

Conti and Siverson's inspiration stemmed from things they loved, like showcasing the flowers from their well-tended gardens. Henning was a fan of hats and used to buy them, but after finding only disappointment in department store selections, she began to make her own.

Steinmann's spark grew from a simple pattern for a felted hat that her mother gave her. As a child, she made clothes for her stuffed animals, and later in life, she sewed her own clothes. After trying the pattern, she began to sell hats locally at a gallery shop on Cape Cod. Now, her site delivers to people all over the world.

From Michigan to Idaho and Ohio to Cape Cod, they craft custom hats for women they may never meet in person.

It means e-mailing photographs and mailing swatches of outfits to match the hats, hours of chatting on the phone and even using software to "try on" a hat (a feature Siverson's website offers) or a virtual "sitting room" with everything from a "millinery mugshot" to photos of the hat in progress on Conti's site.

Siverson and Steinmann chat with their customers, listening for the nuances in their voices. The conversations reveal the kind of hat they want, from reserved to loud and crazy. Because a bespoke hat is such a personal thing, they want the finished product to project the customer's personality.

After investing anywhere from three weeks to an entire year into the making of a hat, a connection forms between the milliner, eager to hear her customer's response, and the wearer, who usually picks up the phone as soon as the box arrives, squealing.

"It is so amazing to pop it into the box after that kind of involved process," Steinmann said. "I not only have a relationship by then with the customer, but the hat as well."

Like the other milliners, the hats featured on Henning's site aren't "sitting on the shelf" and ready to ship. Rather, the photos are inspiration for what customers might want to build. And just about every client asks, "Have you already sold a hat like this for the Derby?"

Inspirations for the hats come from their customers, but Conti is especially influenced by the glamour of 1930s and 1940s millinery. Because she is "creating all the time," Conti can even find inspiration by looking at a bowl or a lamp. For 19 years, she has been creating almost all her hats by hand: "It makes the stitches less easy to see."

Helping a woman find her perfect hat can be inspiring, as veteran Derby hat seller Lucille Jackson, owner of Hunter's Hatters in Lexington, Kentucky, knows well. The 80-year-old has been in business since 1984, but her shop could close after the Derby because her older, loyal customer base has shrunk due to illness and old age.

Although she orders 95% of the hats in her store, she customizes most of them to suit the individual personality of her customers, from one-timers to regulars. "I would rather see a lady happy in a hat that completes her wardrobe than to do a lot of things, honey," Jackson said

But she remains optimistic that she'll stay in business, because Jackson offers the kind of personal, by-appointment service that isn't available in department stores today. She sits down with her "ladies" and helps them determine their color, style and "hattitude," something the milliners are well-versed in spotting.

"You've got to know how to wear it," Jackson said. "You have to have an attitude for a hat, and that creates a hattitude. If you don't have an attitude about the hat, it doesn't mean anything, like a stick pin -- it's just there. A hat is a true accessory and so important, because it makes a woman look so beautiful and feminine."

Have you ever been to the Kentucky Derby? Did you wear an incredible eye-catching hat? Please share your experience in the comments below!

Michael Matz was a member of the U.S. showjumping team that won the silver medal at the 1996 Atlanta Olympics, and more recently a trainer of racehorses. But he will always be remembered for just one: Barbaro.